


The Sugar Baby Mission

by LuciferaBlack



Category: The Blacklist (US TV)
Genre: Alternate Universe - Canon, F/M, Flirting, Fluff and Smut, Porn With Plot, Romance, Seduction, Shameless Smut, Smut, Sugar Baby Lizzie, Sugar Daddy, Undercover
Language: English
Status: Completed
Published: 2020-05-14
Updated: 2020-05-23
Packaged: 2021-03-03 04:20:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 17,435
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24188803
Author URL: https://archiveofourown.org/users/LuciferaBlack/pseuds/LuciferaBlack
Summary: Liz is part of a secret task force and her mission is to gather intel from Raymond Reddington, using any means necessary. She goes undercover as a woman looking for a sugar daddy, with Reddington as her target.
Relationships: Elizabeth Keen & Raymond Reddington, Elizabeth Keen/Raymond Reddington
Comments: 57
Kudos: 99





	1. Making Contact

**Author's Note:**

> I was watching a crime show where there was a young woman after an older rich man's fortune. I also remembered having fun writing the sugar baby mission storyline in my other fic "Deep". This story came to me! Yay for some inspiration!
> 
> Disclaimer: I do not own The Blacklist or the characters, and I do not make a profit. This is strictly for fan entertainment purposes.

Liz was listening attentively to her instructions from Cooper and Ressler. She felt nervous but she’d been trained in undercover work, so she knew she was competent. The anxiety was due to the vulnerability of her undercover role, plus she didn’t want to mess up the mission.

“Agent Milhoan, as you know, this task force is top secret. It can go beyond normal ethics and legalities. Do you fully understand and accept that you are required to gather intelligence from Reddington using any means necessary?” Cooper said.

Liz nodded, then Ressler chimed in.

“That basically means sex, because Reddington has been known to withstand torture, confinement, interrogations, threats and blackmail.” Ressler said plainly.

Liz felt a little embarrassed, not to mention somewhat used, but she nodded again.

“I realize that. I’m prepared to do whatever it takes. I know how important this mission is. I know I’ll be deep undercover for an indeterminate amount of time, and I may have to engage in sexual activities with Reddington.” Liz said.

Cooper sighed; he felt bad for putting her in this position, but she was a dedicated agent and she seemed to be up for the challenge. He handed her the waiver forms to sign, then he reminded her of the safety protocols in case she needed to bail out of the mission.

Liz felt jittery as she left the black site, due to her nervousness; she made sure she wasn’t being followed, then she took a taxi to her new ‘apartment’, which was a safe house for her to use during the mission. It was a nice but modest apartment, all set up and furnished according to her new character. She was now ‘Lizzie Scott’, a college graduate trying to pay off her student loans, and gain security and status. Liz took her blouse and slacks off, then her bra and panties; she put a nightshirt on and went around the apartment, exploring. She looked in all the closets, cupboards and drawers. Embarrassingly enough, the task force left her with scanty clothes, lingerie, condoms, lubricants, and even a vibrator in the bedside table.

“Wow. Thanks, guys…” Liz muttered wryly, then she chuckled.

She then went into the kitchen and helped herself to a yogurt parfait that was made for her. She put the TV on for some background noise, then she chose a dark blood-red nail polish from the collection in her bedroom. Liz painted her fingernails and toenails while she listened to a TV show. After touching up her nails and letting them dry completely, she used her favourite skincare products, which the task force was kind enough to stock up on. Liz got into bed and set her phone alarm. She was comfortable and she actually liked her new apartment, but she had trouble getting to sleep. She mentally went over her instructions, plans, possible scenarios, everything. She wondered if she would even be able to engage Reddington in conversation or capture his interest. If not, the mission would be a non-starter. Liz decided she would just have to do her best and rely on her training, as well as her flirting skills, which she hadn’t used in a while. Hopefully they would come back to her. Tomorrow evening, the mission would commence.

~ ~ ~ ~ ~ ~

Liz was sitting at her dressing table, finishing applying her subtle lip colour, which she thought would look enticing. It was perfect for enhancing her natural lip colour, like she’d just been kissing. She put the tube of lipstick in her purse and checked her appearance in the mirror. She felt confident; she looked pretty and sexy. Definitely flirtatious in the low-cut black sleeveless dress. Liz bent down and put her shoes on, then she glanced at herself one final time before leaving the apartment. She got into the waiting ‘taxi’, which was actually operated by a fellow undercover agent to ensure her security and arrival at the location. It took some time to reach the very upscale swanky gated community. Once the car pulled up to the target mansion, Liz took a deep breath and left the safety of the taxi to enter the mansion and begin her mission.

Liz was greeted by a server and some kind of butler, who hovered around waiting for people to give him their umbrellas, coats, hats, etc. She didn’t have anything to hand over to him, so he went to the next person who entered, which was a pretty young woman—younger and prettier than herself, Liz thought worriedly. She needed to get to Reddington first before someone else got their hooks into him. Liz accepted a cocktail from the server’s tray, then she swiftly made an entrance amongst other partygoers, ahead of the younger woman.

Across the room, Red was standing with his back to the wall, talking to a man about the diamond trade. His attention was captured by a young woman with brownish hair and a beautiful face. He recognized her immediately as Elizabeth Milhoan, FBI agent, and the grown-up version of the little girl he took out of the burning house. He’d kept tabs on her all these years. She was out to get him. Red knew that, and he decided to play along. He would pretend to be oblivious to her true identity. This was going to be a fun game.

Liz scanned the large room and found Dembe first; she recognized him as a known associate of Reddington. Her eyes then landed on the man himself—Raymond “Red” Reddington. The photo the task force showed her had been from quite a while ago. He had less hair now, but he still had the same handsome face, the expensive clothes he was famous for wearing, and the arrogance about him that Ressler said angered him. Liz glanced beside her and saw the younger woman mingling with guests, and she wanted to make a beeline for Reddington but she decided that would be too obvious. Besides, she had to greet people as they introduced themselves to her. She also got a surprise hug from an FBI informant, the man who had agreed to send her an invitation to the party so that she could interact with Reddington.

“Hello Lizzie! Wonderful to see you, so glad you made it.” Calvin said.

Liz had to push aside her first instinct, which would be to either hit him or arrest him. She smiled.

“Hey, there you are. Thanks for inviting me. Great party.” Liz said convincingly.

“Isn’t it? Go mingle, have fun. We have endless booze.” Calvin said, then he took off into a group of people.

Liz watched Calvin for a moment, then she faced forward again. She was shocked to find Reddington standing in front of her, smiling gently. She was almost visibly startled but she managed to keep her cool.

“Hello there. You caught my eye from across the room. That dress is really something…” Red said suavely.

“Oh, thank you.” Liz said, glancing down self-consciously at her cleavage.

She noticed that Reddington indulged in a glimpse too, but then he maintained eye contact like a gentleman.

“I’m Raymond.” Red said, extending his hand.

“Hi, I’m Lizzie. Nice to meet you.” Liz said, shaking his hand.

“The pleasure’s all mine.” He said, then he lifted her hand to kiss it lightly.

Liz didn’t expect him to start working his charm right away; she could see why he was popular with women. This didn’t seem like a cheesy pick-up attempt; he was truly attentive, chivalrous and suave. He was certainly taking the bait.

Funnily enough, Red was thinking the same about her; Lizzie was lapping up his attention, thinking she was in control. She was probably very pleased with herself to think he was falling into her trap so easily. Red was interested to hear what Lizzie’s backstory was; the FBI likely turned her into a sugar baby.

“Tell me about yourself, Lizzie.” Red said.

“Well, I’m an only child, I graduated with a psychology degree but haven’t found a job in the field yet. I like dogs and going for walks, not that I can afford a pet right now. I’m single…and I think Cosmopolitan cocktails taste like nail polish remover.” Liz said lightheartedly, then she put the drink down on a nearby table to get rid of it.

Red laughed heartily.

“I agree.” Red said amusedly; he detected some of the character she was playing, but also some of her true self. He was intrigued by the bits and pieces of her true personality.

Liz smirked.

“I know where to find a terrific bottle of scotch.” He said enthusiastically, gently putting his hand on her upper arm.

“Really?” She asked.

“Yes, it’s down the hall in the other room. Would you care to join me for a real drink?” He said.

Liz felt nervous again.

“Sure, that sounds good.” She said.

“Excellent. Walk with me.” He said cordially, then he escorted her to another room.

Liz’s stomach tightened as Reddington closed the door behind them, but as she watched him go over to a curio cabinet and open it, there was a playfulness about him. He was having fun sneaking this special bottle nobody was supposed to be drinking from. The closed door appeared to be for the purpose of stealing liquor, not for making sexual advances on her. Liz smirked as she watched Reddington crack open the seal and take the lid off. He found two glasses and poured the golden liquid, then he handed her one.

“Whose is this, anyway? Calvin’s?” Liz asked quietly.

“It’s his grandfather’s.” Red said.

Liz’s mouth dropped open; they were stealing and ruining an heirloom from a famed crime family. Reddington just chuckled and sipped the scotch.

“He owes me. I consider this payback. Go ahead, Lizzie, it’s fine.” He explained.

Liz timidly sipped the scotch.

“Wow. It’s better than the cocktail, anyway.” She said.

Reddington laughed delightedly and then gestured for her to sit on the settee with him. They sat down and Liz smiled at him.

“Tell me about yourself, Raymond. You’re very interesting.” Liz said.

“I travel around a lot, I’m independently wealthy. I have ties to some unsavoury characters. Like you, I have a fondness for animals and slow strolls. I enjoy the finer things in life, but also some simple pleasures.” Red said.

“Hm.” She responded interestedly. That was a shockingly honest answer; it was actually close to the truth, and she was impressed. She’d been expecting some story about him being an ordinary guy like a weatherman or accountant.

“How does a seemingly normal college graduate find herself at a criminal’s house party?” Red asked, throwing her a curveball.

“Calvin is the cousin of an acquaintance from one of my college classes. He suggested I should come to one of Calvin’s parties to mingle with people and…maybe meet someone special. He told Calvin to invite me, and here I am.” Liz said.

Red was impressed with Lizzie’s quick thinking and how she kept her stories close to the truth. She was a good liar.

“I see. Most of the men here are what you might call ‘sugar daddies’.” Red pointed out.

Liz chuckled.

“Yeah…I’m okay with that.” She said, smirking.

“Hmm. And here I am, an extremely wealthy, unattached man…” Red said charmingly.

Lizzie giggled and her cheeks looked a bit more rosy.

“And very handsome.” She added.

“Oh, thank you.” He said.

Liz smiled; she wasn’t just saying that for the sake of the mission. Reddington was very attractive. It was a lot easier to flirt with him than she thought it would be. They heard footsteps in the hall and then the door opened. It was Calvin. Liz was startled and backed into Reddington for protection.

Calvin saw the opened antique bottle of scotch on the table and he was livid, but he knew that he still owed Reddington a favour. Because he was an informant, he also knew that Agent Milhoan was on a mission and he shouldn’t do anything to jeopardize it, otherwise he’ll get locked up by the FBI. He groaned and rubbed his face in exasperation, then he shook his head and left the room, closing the door as he went.

Liz realized she was still kind of squished against Reddington on the settee. She turned to look at him. His eyes were even more enchanting up close, and his clean shaven face looked smooth and touchable. His lips looked soft.

“That scared me.” Liz said quietly.

Red wasn’t sure if Lizzie was actually scared or not, but he seized the opportunity. He gently rubbed her arm.

“There’s no need to be frightened, sweetheart. Did you see the way he just left without confrontation? That’s because he knows I’m simply cashing in on a favour.” Red said.

Lizzie looked unconvinced, so he lightly caressed her cheek.

“Don’t worry about Calvin and his liquor. Besides, I would protect you if anything happened. Do you trust me?” He said.

Lizzie nodded and gave him a small smile. Her lips looked luscious and kissable. He caressed her cheek for a few moments longer, then he sat back and sipped some scotch.

“Would you like to leave? We could go somewhere else, or I could drive you home.” Red said.

Liz considered the options; should she go somewhere else with him, or go home and leave him wanting more? She had to show enough interest in him, otherwise she might lose him and wreck the mission.

“Where else could we go?” Liz asked.

“Hm. I know a quiet lounge nearby, where we can drink expensive scotch without having to worry about its rightful owner.” Red said.

Liz smiled.

“Okay. Let’s go there. You have a car?” She said.

“I have someone who can drive us.” He said.

“Ooh. Nice.” She said.

Red smirked and then he got up from the settee. He helped Lizzie up in a gentlemanly manner and escorted her out of the room. He stopped by the front door and collected his hat from the butler, then he waved to Dembe.

“Lizzie, this is my good friend Dembe. He has kindly agreed to drive me around this evening.” Red said.

“Hi, nice to meet you, Dembe.” Liz said, shaking his hand.

“Likewise.” Dembe said; he already knew who she was, thanks to Red’s surveillance of her throughout the years.

The three went out to the parking lot and got into the car; Liz and Reddington sat in the back together. A short while later, they went into a lounge where Reddington knew the owners. Dembe sat at the bar while Liz and Reddington were seated in a cozy private corner booth. They sipped scotch, now guilt-free, and Liz started to relax. She knew she wouldn’t let any mission details slip, even while drinking. She wondered if Reddington would let some intel slip, but she doubted it. He was a master of secrets.

“So Raymond, do you come here a lot? You know the owners.” Liz observed.

“I come here occasionally. I like it, so I’ve invested in the business. That’s how they know me.” Red said.

“Oh, okay. Yeah, it’s a nice place.” She said; again, Reddington’s answer was close to the truth but he wasn’t going to elaborate, so she had to drop the issue.

They sat quietly, sipping their drinks and glancing at each other.

“That really is a lovely dress. You look stunning in it.” Red said.

“Thanks.” Liz said, giving him a coy smile.

“I’m a gentleman, but that plunging neckline…mm. Very tempting.” He said, allowing himself another look at her cleavage.

“Thank you.” She said softly.

Red watched as Lizzie turned towards him and leaned a bit closer, giving him an eyeful of her cleavage. She was eagerly offering him a better view, and he loved it.

Liz was unsettled by how much she liked getting Reddington’s attention. She was excited by the lustful, appreciative way he surveyed her. She found herself becoming aroused. If her mission came to the point where she’d have to use ‘any means necessary’, she’d most likely enjoy it thoroughly. Actually, Liz was pondering getting into bed with Reddington even if it wasn’t necessary. She smirked and giggled flirtatiously, which seemed to please him. He smiled.

“I think you’re really handsome and charming. How are you single?” Liz said.

Red laughed.

“I don’t know how you’re single, either.” Red said.

Lizzie shrugged cutely.

“I’ve been single for quite a while. I don’t mind, but…sometimes I get lonely.” She said.

“Hm. Same here.” He said.

“Maybe we can…keep each other company…” She said suggestively.

“I’d like that.” He said.

Red wondered if any of Lizzie’s flirtation was sincere, and how far she’d be willing to go. His flirtation was definitely real. Lizzie was beautiful and sexy, and he was enthralled with her. He would go to bed with her in a heartbeat if she wanted to.

“I’d like it, too.” Liz said quietly, then she subtly put her hand on Reddington’s thigh.

She was thrilled by the smouldering look he gave her.

“Let me give you my number so we can keep in touch.” Liz said as she caressed his thigh.

“Yes please.” Red said, making her giggle.

He handed Lizzie his burner phone and she added herself as a contact, then she handed it back to him.

“I’d give you mine, but I often get new phones…” Red said.

“That’s okay. As long as you call or text me.” Liz said.

“I definitely will, don’t worry.” He said.

“Good.” She said.

Liz took this moment to go into her purse and get her lipstick out, then she refreshed it using her tiny compact mirror. Reddington watched her like a hawk, and she saw out of the corner of her eye that he tilted his head and looked down at her thighs. Red was appreciating the sight of Lizze’s crossed legs and very short hemline. It left just enough to the imagination. He gave her a cute almost innocent smile when she looked at him. She smirked and put her mirror and lipstick away.

“Do you want a puppy?” Red asked.

“What?” Liz laughed.

“You said you like dogs, but you couldn’t afford a pet right now. Or would that be too much work?” He said.

“Uh…” She responded.

“You know what doesn’t require a lot of maintenance? A diamond necklace.” He said.

Liz was puzzled and surprised; Reddington appeared to be enthusiastically getting into the sugar daddy role already.

“Do you like diamonds, Lizzie?” Red asked.

“Yeah. Who doesn’t like diamonds? They’re gorgeous.” Liz said humorously.

“Wonderful. I know of the _perfect_ necklace for you. It’s got one large teardrop diamond, multifaceted to catch the light brilliantly. It would hang just about here…” He said.

Liz breathed a little heavier as Reddington trailed his fingertip downwards from her collarbone, almost between her breasts.

“Do you want it?” Red asked quietly.

Liz started blushing, and Reddington smirked amusedly.

“The necklace…do you want it?” He clarified.

“Um…it isn’t…stolen or anything, is it?” She said.

Red laughed.

“No. I was given the diamond as a gift—well, more of a trade—and I had it made into a custom necklace. I designed it myself. I love it, but I can’t wear it, it wouldn’t suit me. It would give me great pleasure to see it on you.” Red said.

Liz liked the idea of giving him great pleasure.

“Wow, okay. If you want to give it to me, I’ll accept it. Thank you so much.” Liz said.

“Fantastic. I’ll give it to you tomorrow. We could meet up again, or I could drop it off, whatever you’d like.” Red said.

“I’d like to meet with you again.” She said softly.

“Lovely. How about for now, I drive you home.” He said.

“Okay. Thanks.” She said.

Liz followed Reddington to the door, then he held the door for her and she went out first. Dembe followed them and the three got into the car. Liz gave them her address, which was her newly acquired safe house apartment. Good thing she remembered the address. They pulled up to the building.

“I’ll walk you to the door.” Red said.

Liz smiled and they walked together to the front door.

“I’ve had an amazing time. Thanks for everything, Raymond, and I look forward to seeing you tomorrow.” Liz said.

“You’re very welcome, Lizzie. It was a splendid evening.” He said.

Liz had butterflies in her stomach as they looked at each other, but then she leaned in and kissed Reddington on the lips. They were both surprised; Liz was perhaps getting a little carried away in her role, but it felt good. He gently cupped her cheek in his hand and returned her kiss. It lasted for several long moments, and Liz felt almost dizzy when it ended. Reddington was an incredible kisser. It had been slow, erotic and tantalizing. She wanted to continue.

“Goodnight, sweetheart. I’ll call you tomorrow.” Red said.

“Yes. Do that. Um…goodnight, Raymond.” Liz said, feeling somewhat dazed and flustered.

Red put his hat on and went back to the car. He rode home to his safe house feeling encouraged. Lizzie’s steely determination as an undercover agent seemed to be no match for her attraction to him. He wasn’t sure what her mission was, but it was either to capture him or just gather intel. Whatever it was, he would make her fail at it, using her own strategy against her—seduction.

~ ~ ~ ~ ~ ~

A while later, Liz got into bed. She thought about how the start of the mission went. She felt pretty good about it, because she captured Reddington’s attention and started a relationship with him. She might’ve gone too far by kissing him already. Liz vividly recalled the way Reddington’s lips moved, and his tongue barely trespassing between her lips. She remembered she had a brand new vibrator in the night table, so she reached over and took it out of the drawer. She turned it on and lightly held it against her clit.

Meanwhile, Red was wondering what Lizzie was up to right now. He used a hacking device he was given by some hacker kid to tap into her cell phone, using her phone number. It turned the microphone on so he could hear if she was telling the FBI about him. Instead, he was confused by a quiet buzzing sound. He thought the hack wasn’t working, but then he heard Lizzie moan. He immediately realized what was going on; she must’ve had the phone nearby while she pleasured herself with a vibrator. Red soon became fully erect, and he couldn’t resist masturbating while listening to her. He pulled down his boxers and began pumping his cock. He heard Lizzie whimper.

Liz teased herself by moving the vibrating tip in circles around her clit, then holding it against her opening to give herself vibrations inside.

“Ohhh…Raymond…” Liz moaned softly; she was picturing his cock rubbing her and nudging her.

Red couldn’t believe his ears; Lizzie was fantasizing about him. That wasn’t a performance as her undercover character; she didn’t know he would hack into her phone and listen. He pumped his cock faster, just under the head of it, and he heard Lizzie mewl and breathe heavily as she orgasmed. He grunted and his semen spurted out repeatedly as he came. Red heard Lizzie sigh and then the buzzing stopped as she turned the vibrator off. He disconnected the hacking device and used a towel to tidy himself.

Liz tiredly put the vibrator on the night table and sprawled out relaxedly. She was satisfied, although she would’ve preferred experiencing Reddington for real.

(To Be Continued…)


	2. The First Move

The next day, Liz couldn’t stop thinking about Reddington. She felt guilty for being attracted to him and fantasizing about him; she knew that wasn’t professional of her, but on the other hand, it made her mission easier. She wouldn’t have any problem with getting closer to him. Liz chose a sexy little ruffled skirt and form-fitting tank top from her closet and waited around for Reddington’s call. Finally, in the afternoon, her phone rang and she excitedly answered it.

“Hello?” Liz said.

“Hello Lizzie, it’s Raymond. I picked up the necklace for you. I can’t wait to see you wearing it. May I come over to your apartment?” Red said.

“Sure! I’m really excited. Come over.” She said.

Red wondered just how excited Lizzie was, and he smirked.

“I’ll be right there.” He said, then he hung up.

Liz felt nervous and she went around the apartment tidying it up, but she realized everything was already in its place and none of her own personal belongings were there. It was full of props for her character. She calmed down slightly, but her heart raced again when the apartment buzzer sounded. Liz pushed the button and waited for the knock on her door, then she let Reddington in.

“Hi!” Liz said, ushering him in.

“Hi. Wow, you _are_ excited. Well, here it is. I hope you like it.” Red said amusedly, then he lifted the necklace from his jacket pocket and held it in front of her.

“I’m excited to see _you_ , silly. But yes, the necklace is amazing. It’s so beautiful. I’m not sure I can accept it after all.” She said; she felt bad for lying to Reddington. He was giving her a special, personally designed custom diamond necklace under false pretences.

“I want you to. Please accept it. It’s meant to be worn and enjoyed.” Red said.

Lizzie shyly nodded, which pleased him.

“If you’re sure, okay. Thank you.” She said.

“You’re welcome. May I put it on you?” He said.

“Yes.” She said.

Liz saw the diamond catch the light in an array of colours as it dangled from Reddington’s hands. She turned around and he brought it in front of her, then she shivered subtly as the delicate chain tickled her neck. He fastened the clasp at the back of her neck, then his fingers ran down her back a little bit. Liz got a thrill from the sensation.

“There.” Red said softly.

Liz turned to face him again.

“Breathtaking.” He said appreciatively.

“Thank you. It’s gorgeous.” She said, looking down at the diamond pendant.

“You’re gorgeous.” He said.

Liz looked up and smiled.

“Thanks.” She said.

Red then took a moment to survey Lizzie.

“I didn’t take you for a pink frilly mini-skirt type of gal.” He said amusedly, knowing full well that this was one of her undercover costumes.

“I found it in the closet and threw it on…I don’t wear it often.” Liz said; she literally found it in the closet.

Red smiled.

“You look sexy in it, if you don’t mind me saying.” He said.

“I don’t mind. I’m glad you think so. Can I get you anything?” She said.

“Perhaps just a glass of water, thanks.” He said.

“Coming right up.” She said, then she got a glass and filled it with cold filtered water.

Liz returned to Reddington and their fingers touched as he grasped the glass. They smiled at each other.

“Would you like a tour?” Liz offered confidently.

“Sure.” Red said.

“You’ve seen the kitchen. Here’s the dining area and the living room. The view is pretty nice from the window. I like to watch the sunset sometimes.” Liz said.

“How long have you lived here?” Red asked.

“Five months.” She said; really it was her second day here.

“Did you move far to come here?” He asked; he was curious about what stories she would weave.

“Not really, I lived about half-hour from here, in a more student-type apartment building. I came here to start my professional life, but like I said, I haven’t found any work in my field.” She said.

“Hm.” He responded interestedly.

“Down here is the bathroom, it’s kind of small but that’s okay.” She said.

Liz led Reddington into the bedroom.

“And this is the bedroom.” She said.

Liz noticed the vibrator on the night table, rushed over to it and hurriedly shoved it in the drawer, then she whirled around to face Reddington. She was blushing.

“Um, that’s embarrassing! Sorry!” Liz said.

Red chuckled.

“It’s quite alright.” He said humorously.

“…I thought I put it away. Oh my god, I’m so embarrassed.” She said.

“Lizzie, relax. It’s not surprising for a single woman to have something to…satisfy her urges.” He said.

“Can we just go back into the living room?” She said wryly.

“Of course!” He said, then he chuckled as they left the bedroom.

They sat on the couch together and Liz giggled embarrassedly.

“I don’t really know what to say now.” She said.

Red put his glass of water on a coaster on the coffee table, then he turned towards Lizzie, resting his arm on the back of the couch.

“You don’t have to say anything.” Red said.

Lizzie smiled.

“I have something to say.” He added.

“What.” She said.

“I found it rather titillating, to discover you use a toy when you’re feeling horny. It turns me on.” He said.

“ _Oh_.” She said dreamily; she was getting turned on now, too.

“Do you…if you don’t mind me asking…use it often? I have quite a healthy sexual appetite myself.” He said.

Liz’s mouth dropped open slightly.

“Um…actually, I just got it the other day. I…used it last night…” She admitted.

“Mmm.” He responded, intrigued.

“I don’t normally use a toy, but it was handy, and I wanted a quick easy orgasm after you dropped me off.” She said flirtatiously.

“Oho! Lizzie, you’re having fun teasing me now, aren’t you?” He said playfully.

“I don’t mean to tease you.” She said coyly.

“Perhaps not. But I wish I would’ve taken you home with me last night. You wouldn’t have needed to use your toy…” He said.

Liz bit her lip excitedly.

“I wish that, too. I actually thought about you while I was using it…” She said softly.

Red was astonished. Lizzie was confessing the truth.

“I pleasured myself while thinking about you last night.” Red said.

Liz was so aroused, she made a kind of tiny whimpering sound in response. She looked down and Reddington’s trousers were tight over his semi-erection. She felt like she just gushed into her panties. Liz suddenly leaned closer and captured Reddington’s mouth in a heated kiss; she put her hand on his chest and moved it down to cup his hard bulge. He moaned quietly into the kiss, which turned her on even more.

“Mm…Raymond…” Liz purred breathily as she rubbed his manhood through the soft material of his trousers.

Red kissed Lizzie and put his hand between her knees; he felt her legs open, and he slid his hand up to her hot, wet crotch. Her panties were practically soaked. He rumbled approvingly and pressed the pads of his fingers against her. She spread her legs wider and gently ground her hips against his hand. Liz was craving Reddington so badly, it was like she was driven purely by lust right now. She couldn’t think of the mission or anything else, she just wanted him. His fingers wiggled on her firm clit, making her whimper.

“Lay back, Lizzie.” Red said intensely.

Lizzie reclined on the couch, with her legs closest to him. He reached under her frilly skirt and pulled her panties down to her knees, then she lifted her legs so he could take them off for her. They were indeed soaked. He dropped them on the floor and then lustfully grasped her hips, pushing the frilled fabric up to reveal her intimate area. Liz opened her legs to Reddington and he put his face between her thighs, where he started licking and sucking her sensitive flesh.

“Ohh god…” Liz moaned breathily.

Red was hooked on Lizzie’s intoxicating scent and taste. He enthusiastically rubbed her very hard clit with his tongue and dipped into her opening. He suckled her inner lips and she ran her hand over his head. When he went back to her clit, she trembled and tensed up, whimpering sweetly in bliss. Liz felt guilty again; she had Reddington’s necklace around her neck and his tongue between her legs. She wasn’t doing this for intel. She was doing it because she wanted to. Liz felt Reddington suck her clit and then flick it with his tongue. She quivered and then mewled as she reached her orgasm. Red was thrilled as Lizzie squirmed with the waves of her climax. He almost came in his pants.

“Wow…” Liz said breathlessly.

Reddington stopped and rose up to look at her.

“I could do that all day.” He said, having thoroughly enjoyed it.

She giggled and pulled her mini skirt down.

“I wanna return the favour.” Liz said lustfully.

“You don’t have to, sweetheart.” Red said.

“Please.” She said, reaching for his belt buckle.

Red didn’t want Lizzie to feel obligated, but she didn’t appear to. She licked her lips and rather urgently undid his belt and pants to get at his erection. She opened his trousers and excitedly pulled his cock out of his boxers. Liz moaned lustfully as she gazed at Reddington’s cock, then she took him into her mouth. She heard a low groan from his throat, which turned her on. She moved her hand up and down his lower shaft and her mouth glided over the head of his cock and down to about midway. Liz tightened her lips and went faster as Reddington’s breathing became heavier. He petted her hair and put his fingers into it. She could tell his need for satisfaction was increasing because of his breathy moans, and the taste of his pre-ejaculate fluid.

“Oh, Lizzie…” Red breathed.

“Mm.” Liz whimpered excitedly.

She went faster, bobbing up and down, and Reddington squirmed slightly, gently bucking his hips.

“Yes…oh fuck…” He whispered.

Liz was ecstatic. She slowed down a little and took him deeper into her mouth, then she went up and sucked his tip. He groaned desperately. Liz resumed the quick, tight movements and Reddington lightly grasped her hair.

“Baby…I’m going to come…” Red said breathlessly.

“Mmm!” Liz moaned sexually; she was excitedly awaiting it.

Red felt Lizzie increase her efforts, going faster, and several moments later, he reached the pinnacle of ecstasy. His breath caught and he grunted as the intense pleasure hit him; he started coming in her mouth. Liz almost climaxed along with Reddington. His cock throbbed and his semen spurted into her mouth again and again. It stopped and she gently sucked him before swallowing, then she lifted up and looked at him. He had the most satisfied expression on his face, so she giggled delightedly.

“Did you like that?” Liz asked playfully.

She gently tucked him back into his boxers.

“My goodness. Yes.” Red said in a daze.

Liz felt pangs of guilt once more, because she hadn’t gotten any intel from Reddington yet. They were just flirting and fooling around. She tried to reassure herself that intel might come later, as a result of their intimate relationship. She ran her fingers through her hair and flipped it over to cool her face and neck. Red gazed at Lizzie, who was flushed and somewhat preoccupied.

"Are you alright?" Red asked. 

"Yeah, totally! I just got lost in thought for a moment." Liz said. 

"Are you stressed?" He asked. 

"Not really." She said.

Reddington tilted his head and studied her.

“What else do you need? Loan payments? A new apartment? I’d love to help you and pamper you, if you’ll let me.” Red said; he was curious to see how far Lizzie would go in her sugar baby role, plus he truly wanted to lavish her with attention and gifts.

“Um…” Liz began.

“Perhaps more jewelry…and adorable skirts.” He said lightheartedly.

“Well…” She said.

“I know what I can do for you. I can whisk you away on a weekend trip to a private island. Do you own a bikini? If not, we can sort that out.” He said.

“Wow, this is all very nice of you to offer…but can I think about it?” She said.

“Of course. I realize I may come on a little strong, but we’re both single, and you said you couldn’t afford certain things. I’m in a position to take care of you, Lizzie.” He said.

“…I like the idea, I just need to decide what you could help me with. I think the weekend getaway sounds amazing. When would we go?” She said.

“Three days from now, by private jet.” He said.

“Oh! Okay, um…can I answer you tomorrow?” She said; she wanted to check with the task force before going on a trip with Reddington.

“Absolutely. I don’t mean to rush you, sweetheart. I’ll let you think on it. I actually have some business to attend to, if you don’t mind me taking off. I’ll just use your bathroom first.” He said.

“Okay.” She said.

Reddington went to use her bathroom and she was wondering what to do. She wasn’t sure which things would be okay to accept from Reddington—if anything—and whether she’d gone too far already. She also didn’t know how to handle a weekend trip, since that wasn’t in any of the task force’s contingency plans. Liz never had anyone whisk her away for a weekend before, or give her a diamond necklace; nor did her previous partners turn her on as much as Reddington did.

“Before I go, I have something else in my pocket for you.” Red said as he returned to the living room.

“Oh, really?!” Liz said in surprise.

“Yes. It’s your very own prepaid credit card with ten thousand dollars on it, just as a treat.” He said.

Liz nearly fainted.

“Seriously? That’s quite the ‘treat’!” She said in astonishment.

“Well, it’ll get you a couple of alluring bikinis and sarongs, and whatever else you might want, like an espresso machine or whatnot.” He said jovially.

Liz was wondering where Reddington shopped that a couple bikinis, sarongs and an espresso machine would cost ten grand. She gaped at him.

“Uh thank you! I don’t know how to thank you enough. You’re too generous, Raymond.” Liz said.

“It’s not a big deal. Not to me, anyway. Enjoy it! And I’ll be in touch tomorrow.” Red said, then he bent down and kissed her before making his way to the door. He put his hat on and left.

Liz was stunned for several long moments, then she sprang into action. She reached into the secret compartment of the window sill and took out a special separate burner phone, then she texted Ressler: _Need to meet, 10 minutes._

She realized she needed to put some panties on, so she did, then she grabbed her purse and left the apartment, wandering around and going into a convenience store first to make sure she wasn’t being followed. Liz went a few streets over and met Ressler in a pedestrian tunnel. He ignored her sugar baby outfit, but he definitely noticed the necklace.

“Do you need to bail out?” Ressler asked.

“No. I don’t think so, but…he wants to take me on a weekend trip in three days to some private island!” Liz said.

“Go for it. We can extract you if necessary. Has he given you anything yet?” He said.

“He’s given me everything _but_ intel so far…” She said.

“It’s early. He doesn’t trust easily, it could take a long time. Hang in there.” He said.

At first, Liz felt somewhat abandoned by the task force, but as she thought about it, this meant she was free to basically do whatever she wanted with Reddington, wherever, and for however long. That sounded kind of fun.

“Okay. I’ll keep going. Thanks.” She said, then they parted ways.

Liz was walking home on a long, winding route to lose anyone tailing her. She glanced beside her at the storefront windows and saw a very revealing, barely-there light blue bikini. She remembered she had a prepaid credit card in her purse. _Dare I?_ She thought. It wouldn’t hurt to see if they had her size. Liz entered the store. A short while later, she emerged with a bag containing the light blue bikini, a yellow and blue sarong, and a straw hat. She felt both guilty and elated as she took her bag of boutique goodies home with her.

(To Be Continued…)


	3. Losing Themselves

Liz kept busy the next day, planning and preparing for different scenarios that might occur during the trip with Reddington. She couldn’t make any notes in case he found them at some point, so she went over everything in her mind. Time flew because she was so preoccupied. She decided to take a break and incorporate some mindfulness into her day. Liz went into the bathroom, undressed and carefully took off her diamond necklace. She examined it again, and it was stunning; she delicately placed it on her storage shelf and got into the shower. She focused on the soothing warmth of the water as it sprayed her skin, and she let her mind go blank as she massaged her scalp while lathering the shampoo. Liz paid attention to how her favourite bath products smelled, subtle and sweet; after rinsing, she massaged her shoulders and let the warm water loosen the muscles in the back of her neck. She sighed relaxedly and turned the water off, then she got out and dried herself. Liz used the hairdryer and put body lotion on, then she got into some pyjamas. She chose to wear the black tank top and shorts set with red hearts all over them. She put her necklace on the bedside table. She realized it was one of her prized possessions, and she felt sad at the thought of either Reddington taking it back when he found out the truth or the task force seizing it.

Liz sighed as she pondered her situation. She would’ve liked to meet Reddington under different circumstances because he was charming, intriguing and fun to be around. But she was on a mission. Liz felt ready to give Reddington her decision about the trip, but she had to wait for him to call since she didn’t have his number. She took her phone with her as she lounged in bed, starting to read a book that was on her bedside table. She read several pages and got absorbed in the budding romance between the characters. Her phone rang just then, so she put the book down and answered it.

“Hello?” Liz said.

“Hello sweetheart, sorry I didn’t call sooner. Have you given any thought to the island trip?” Red said.

“Yeah, I’m coming with you!” She said excitedly.

“Wonderful!” He said happily.

“And guess what. I even bought a bikini, a sarong and a hat.” She said.

Red chuckled delightedly.

“Excellent. I can hardly wait to see you in them. I’m hoping the bikini is skimpy.” He said.

Liz giggled.

“It is!” She said.

“Mm. Lovely.” He said.

“I used the card you gave me. Thanks again, Raymond, you’re so sweet.” She said.

“You’re more than welcome.” He said.

“What else should I bring?” She asked.

“Oh, anything you think might add to the fun. We’ll have the finest luxuries and amenities, of course.” He said.

Liz bit her lip excitedly; she would empty the night table drawer of lubricants and condoms and put them in her suitcase.

“Okay. Will I see you before the weekend?” Liz said.

“Unfortunately, I’m taking care of some business to clear my schedule for the trip.” Red said.

“Oh. Serious stuff?” She said.

Red smirked; this was Lizzie’s first attempt at gathering intel from him.

“No, nothing major. It’ll be done in time for the weekend, don’t worry.” Red said.

 _Well that failed,_ Liz thought wryly.

“Okay, good!” She said.

“Yes. I would never leave my sweet little sugar baby high and dry.” He said indulgently.

Liz couldn’t help giggling.

“I’m your sweet little sugar baby now?” She asked playfully.

“Of course you are, you saucy minx.” He said.

Liz laughed amusedly.

“Thanks. I’m honoured. Um…you don’t have any other sugar babies, do you?” She said.

“No, you’re my first. You’re the only one worth spoiling. I don’t give my time and affection to just anyone.” He said.

“Hm. I really _am_ honoured! I’m glad I have you all to myself…” She said flirtatiously.

“You’ll have me all to yourself this weekend. We’ll be the only people on the island.” He said.

Liz swallowed nervously, but she recalled Ressler saying they could extract her if necessary.

“Sounds amazing.” She said.

“I’m looking forward to it. Well, I’d better go, Lizzie. I’ll pick you up at two p.m. on Friday, out front of your apartment.” He said.

“Okay. See you then, Raymond.” She said.

“Indeed.” He said, then he hung up.

Liz put a reminder in her phone of the time so she’d be packed and out front by two on Friday.

~ ~ ~ ~ ~ ~

It was Friday and Red was on his way to pick up Lizzie. He’d gotten his business settled and now he was free to enjoy the weekend. He pondered Lizzie the whole ride there; she was a good undercover agent, but there were things she couldn’t pretend…Things that signalled her attraction to him. She couldn’t make herself blush on command, or make herself that aroused while engaging in sexual activities with him. He vividly recalled how wet she was, and how hard her clit was against his tongue. On top of that, when he hacked into her phone’s microphone, he heard her moan his name while using her vibrator. Lizzie was genuinely attracted to him; he wondered whether her feelings jeopardized her mission or made it easier. Because she enjoyed being intimate with him, she’d have no qualms about being his lover, his partner…and then what? Turning him in to the FBI? Gently coaxing intel out of him with sex? Red was worried he might actually fall for it. Oh well, at least he’d have fun, sexy memories to keep him company when he’s in a black site for the rest of his life.

Red’s chauffeur pulled up out front of Lizzie’s apartment building and she was smiling broadly, waving at him and wearing her diamond necklace. She looked really excited. He got out of the car and greeted her with a gentle kiss.

“Hi sweetheart.” Red said softly.

“Hi. I missed you.” Liz purred.

She wrapped her arms around his neck and kissed him passionately while the chauffeur put her luggage in the trunk. Liz felt Reddington’s hands go down her back and grope her butt cheeks for a moment, which made her giggle.

“I missed you too. Mmm you look delectable.” Red said, nuzzling into her neck and holding her waist.

Lizzie was wearing a pair of tiny tan-coloured shorts and a white tank top, which showed some of her bra through the thin material.

“Ohh…thanks.” Liz said breathily; she was dizzyingly attracted to Reddington and after not seeing him for a couple days, she wanted to jump him right here on the sidewalk.

Red could also barely resist getting explicitly sexual with Lizzie in public, so he ushered her into the back seat of the car and got in next to her. He closed the door and the chauffeur began driving to the secret area where his jet was waiting. Liz couldn’t even pay attention to where they were going because Reddington was making advances. He moved closer and caressed her cheek, then his lips brushed against hers, enticing her to kiss him. Liz moaned quietly when she felt his hand rubbing her thigh as they made out. His hand traveled inwards and went between her thighs. His hand didn’t quite reach her crotch, and she wanted him to touch her there, so she opened her thighs a little. Liz was extremely aroused and she wantedsatisfaction, but the chauffeur was right there in the front. She sighed longingly.

“We should wait…” Liz whispered.

“Okay, baby.” Red said, and he stopped.

Liz thought this was the right thing to do, but she immediately missed the stimulation; it was anti-climactic—literally. She looked at Reddington and felt sexually frustrated. She moved closer and put her mouth to his ear.

“Can you touch me again? I want more.” Liz whispered.

Red was thrilled and amused; Lizzie couldn’t stay away.

They tried to be as subtle and discreet as possible, so Liz moved behind the driver’s seat, and Reddington sat very close and leaned towards her. He was blocking the view the chauffeur might have from the rear-view mirror. He kissed her cheek and nuzzled the side of her face while his hand returned to her crotch.

“That’s better, isn’t it…” Red said very quietly in her ear.

“Yes.” Liz breathed.

Red made little movements with his fingers, pressing and wiggling on her clit. She breathed heavier, especially when he kissed her neck while playing with her. Red could hear Lizzie’s quick breathing and he wiggled his fingers faster. She was being quiet, but he heard a tiny gasp and felt her tense up; he looked at her face and she had a look of ecstasy. Lizzie just orgasmed.

“You’re beautiful.” Red rumbled in her ear.

“Thank you.” Liz said softly, then she giggled.

“Anytime you want satisfaction, let me know.” He teased.

“I meant thank you for the compliment…but okay.” She said humorously.

Red chuckled and moved over to his side of the seat.

“We’re almost at the airfield.” He said.

“Oh, already? Okay.” She said, looking around; she felt like she probably should’ve paid attention to where Reddington kept his jet. Oh well, it wasn’t the most vital intel anyway.

They were in a nondescript wooded area and they drove into an open field; the jet came into view. There was a pilot waiting.

“Here we are, Lizzie. Let’s get aboard, shall we?” Red said.

They exited the car and the chauffeur took their luggage to the jet for them, which was a luxury Liz had never experienced before. Reddington gestured to climb the steps first, so she went ahead of him. He no doubt enjoyed the view of her butt. She stepped inside the jet and was awestruck by it. She’d never seen a private jet. It was so nice. Liz realized she’d stopped right in front of Reddington, so she chuckled and moved out of the way.

“This is amazing.” She said.

“Yes, it’s great. Well-suited to my needs, including this little trip. There’s a bathroom down there, drinks cabinet, safety equipment, pillows, blankets, sleep masks, and headphones.” He said.

“Wow. How long is the flight, by the way?” She asked.

“Only about ninety minutes.” He said.

Red knew he just gave a good approximation of the location of his private island to an FBI agent, but he couldn’t really lie about it. Besides, he found himself wanting to comfort Lizzie by telling her it’s a short flight, so he did.

“Oh, not long at all! Where do you want to sit?” She said happily.

“Over here is my favourite spot. I usually get the best views.” He said.

Liz smiled and sat next to Reddington. She was really excited for the flight and discovering a private island, and spending more time with him. If she weren’t on a mission, it would be the vacation of her dreams. After takeoff, she watched out the windows but eventually she just rested her head against Reddington and had a nap. Red enjoyed having Lizzie cuddled up to him, sleeping. He carefully turned and looked at down at her face, and he smiled slightly. At one point, she snored and woke herself up.

“Sorry.” Liz said.

“No need to apologize. We’ll be there shortly.” Red said amusedly.

Lizzie leaned over him to look out the window, curiously watching where they were going. There were sandy shores of nearby islands, and the ocean, and gradually they reached a stretch of road where the jet landed. There was barely enough room for an airstrip, but the pilot managed to stop before they ran out of pavement. The rest was grass, sand, some trees and the ocean.

“There are buildings here, right?” Liz asked.

Red laughed.

“Yes. As promised, there is a small resort area with all the modern amenities. There aren’t any people staying here, but I arranged for fresh food and supplies to be brought. We’re all set for the weekend.” Red said.

“Awesome.” She said.

They took their own luggage this time and made their way around the bending shore to a white stone building. Red held the door for Lizzie and they went inside together.

“Wow, this is so cool.” Liz said.

The building looked like a 5-star resort, only they had it all to themselves. It was bright, clean, spacious, with beautiful decor and bowls of fresh tropical fruits like pineapples and mangoes. Liz was dazed as she followed Reddington around; there was a small heated indoor in-ground pool, lounge room with a fireplace, patio overlooking the ocean, and the master bedroom was something out of a romance novel. The beachy breeze lightly blew the sheers around the vast French doors, the king-sized bed was immaculate and inviting, and the en suite bathroom was not only convenient but opulent.

“I don’t even know what to say.” Liz said, finally turning her attention back to Reddington.

“That you like it?” Red suggested hopefully.

"I love it. I’m blown away.” She said.

“Good! Now let’s eat.” He said.

“Okay.” She said, then she followed him into the kitchen.

They explored the fridge, freezer and cupboards and decided on the fresh chef-prepared seafood salad with fruit salad for dessert, along with some sweet ice wine. After supper, they sat in the living room and continued sipping ice wine. Liz listened to the sounds—and silence—of being on a private island, and she laughed in amazement. Reddington was surprised.

“What?” Red asked.

“There’s no traffic…no neighbours…no sirens…it’s unbelievable.” Liz said.

“Yes. I find that this is the only way to truly escape the hustle and bustle.” He said.

Liz decided she would never tell the task force about this place, even if she knew the coordinates. She wouldn’t have the heart to take this perfect piece of paradise away from Reddington. She put her wineglass down on the coffee table and slumped relaxedly into the sofa. Red amusedly watched Lizzie sort of melt into the sofa with her eyes closed and a smile on her face.

“I’ve never been so relaxed in my life.” Liz said dreamily.

“Good. Let’s just take it easy and settle in. I might even doze off for a while.” Red said, getting comfy.

They stayed quiet and enjoyed the easy, comfortable silence between them. As they started falling asleep, Liz curled up against Reddington and used him as a pillow. A while later, Liz woke up mostly on top of Reddington. She felt perfectly cozy resting on him; he was warm and he had a subtle exotic masculine scent. She didn’t know what products he used, but whatever they were, they drove her crazy. Liz put her nose against his shirt and breathed in, then she sighed and hugged him. Red awoke to Lizzie hugging him while she was laying on him. He smiled and embraced her.

“I didn’t mean to wake you up, I just wanted to hug you.” Liz said.

“That was the best way to wake up.” Red said.

Liz giggled softly.

“Lizzie…” He began.

“Hm?” She responded.

“Do you have any other sugar daddies?” He asked; he figured she probably didn’t since she was on some sort of mission, but he wanted to check anyway.

“No. You’re my first, and my only one.” She said.

“Mm. So this is a first for both of us.” He said.

“Yeah. Do you like it?” She said.

“I love it. How about you?” He said.

“I love it too.” She said.

“Fantastic. How else can I spoil you? I’ll pay off your student loans if you give me the account numbers.” He said.

“Oh, um…no, that’s too much, but thank you.” She said; she didn’t have any loan accounts in her undercover character’s name, only real ones.

“…I’ll give you cash, and you can apply it to your loans.” He suggested.

“Um, you’re incredibly sweet Raymond, but really, you don’t have to do that. You can spoil me with your attention instead…” She said, then she flirtatiously rubbed his chest and put her leg over him.

“ _Oh_ …” He responded interestedly.

“Yeah.” She said, then she kissed him.

Red felt Lizzie start to rub herself against his upper thigh, and he grabbed her butt and pulled her in line with his bulge. She whimpered quietly and they dry humped for several moments.

“Do you…want to try out the king sized bed, Lizzie?” Red asked; he wasn’t sure if she’d agree to go all the way yet, but he’d be happy to fool around again.

“Mmm. _Yes_.” Liz moaned as they rubbed together; she could feel how hard he was becoming, and she was craving him badly.

“Alright, baby…let’s go…” Red said breathily.

They were reluctant to stop and lose the momentum of their pleasure, but Liz got up and Reddington followed her into the master bedroom. She blushed lightly as she took her tank top and shorts off. They watched each other undress bit by bit. Red was staring admiringly at Lizzie’s breasts as she tossed her bra aside, then he took his trousers off. He was wearing his undershirt and boxers while she was just in her panties. He was pleasantly surprised when Lizzie took her panties off, getting completely naked.

“…Before I get naked, you should know that I have burn scars on my back…severe ones.” Red said.

“That won’t bother me.” Liz said earnestly.

Red nodded appreciatively, then he took his undershirt off. Lizzie lustfully surveyed his chest, then she stared at his semi-erection as he dropped his boxers to the floor. She quickly crawled onto the bed.

“Kiss me.” Liz purred seductively as she laid back.

Red got on the bed and crawled overtop of Lizzie to kiss her. She moaned and pulled him closer, so he lowered himself and settled between her thighs. His shaft pressed against her intimate flesh.

“Mm…Lizzie…” Red rumbled.

“It feels so good.” Liz said breathily as she wriggled and humped him; she could easily climax like this.

Liz ran her hands up Reddington’s back and held his shoulders as she arched up against him.

“I brought…lube and condoms…” Liz said weakly, dazed from the pleasure.

“Hm.” Red responded, intrigued; he looked at her.

“But I’d prefer no condom…I have a clean bill of health and I’m on birth control.” She said.

Liz blushed as Reddington gave her a surprised look.

“Really? Well then…let’s do it without. I have a clean bill of health, too. My doctors obsess over my health.” Red said.

“Good.” She said.

They began kissing passionately while they resumed humping each other.

“Do you want to get the lube?” Red asked.

“I don’t think we’ll need it…” Liz said; she could tell she was soaking wet.

“ _Ohh_ …let me feel you, baby…” He said, then he reached down and guided his tip to her inner lips; he slipped between them and became coated with her wetness.

Liz moaned from the exquisite sensation of Reddington’s warm, slippery tip rubbing and nudging her opening. She was relaxed and extremely aroused, so she tried to push down onto him. She whined when it didn’t work.

“Alright sweetheart, do you want it?” Red said quietly as Lizzie became desperate.

“ _Yes!”_ Liz mewled.

Liz felt Reddington press inside her and they both moaned. He gently moved in and out, gradually going deeper. He felt perfect. They fit together like they were made for each other, and their level of attraction was extraordinary. They aroused each other so much, it was intoxicating. Liz hadn’t gotten any intel from Reddington and she was screwing him anyway, but she didn’t care at the moment. She hadn’t been able to resist any longer. Red felt like he was in a fantasy, but it was really happening. Lizzie was pulling him closer, moaning and moving her hips to meet his thrusts. He began thrusting steadily and Lizzie’s slick walls hugged his cock. She whimpered and clutched his lower back, encouraging him to go harder and faster.

“Oh god…Raymond…mm!” Liz mewled in bliss.

Red groaned in response.

“You’re so wet…fuck, it’s so good…” Red said intensely.

This made Liz even wetter; Reddington was slipping against her walls with the perfect balance of lubrication and friction. The head of his cock rubbed her g-spot with every thrust. She felt herself quivering and tensing up, becoming tighter on him. Red was thrilled; Lizzie was whimpering and panting, and she was tightly pumping his cock. Liz was in ecstasy as Reddington’s thrusts became quicker; he was stimulating her g-spot almost constantly. Several moments later, she gasped and cried out loudly as she felt the first wave of her orgasm suddenly overwhelm her. Red paused, otherwise he would’ve come, too. Lizzie writhed and her walls gripped his cock as she orgasmed.

When Liz settled down from her climax, she realized Reddington hadn’t peaked yet. She looked at him and hoped he was going to continue.

“Want to change positions, Lizzie? I’d love for you to be on top.” Red said, catching his breath.

“Yeah!” Liz said eagerly.

Red rolled over with Lizzie, and she giggled. She put her hands on his chest and straddled him. She moaned and her hips gyrated as she got horny again.

“Yeah, that’s it baby…” Red said, gazing at her breasts.

Lizzie pushed down on him, taking him very deep, and she arched her back and mewled softly. Red watched her experiment with different movements, then they got into a rhythm together. He held her hips and guided her up and down on his cock. They went faster and he bucked his hips to thrust into her each time. Liz was heading for a second climax and she could tell Reddington was getting close too, now that he was letting loose. She was practically bouncing on him, and they were both breathless and frantic. Red was relishing the eye candy as Lizzie’s breasts bounced. She had a blissful expression and she was losing her rhythm; she remained tense, then she moaned loudly as she achieved her orgasm. He immediately started coming. Red held Lizzie down and groaned as he spurted repeatedly inside her. They were both in the throes of intense pleasure as their bodies throbbed together. Liz felt herself continuously clamping down on Reddington’s cock, which felt good; she could also feel a subtle pulsating as he came in her. It was the sexiest thing ever. She’d never been so gratified.

Liz hummed softly in satisfaction and she leaned forward, placing her hands on either side of Reddington’s head.

“You are so hot. Oh my god.” Liz purred, then she giggled happily.

“Thank you. So are you. That was _astounding_.” Red said dazedly.

Liz became giddy and she giggled as she kissed him, then she nuzzled into his neck.

“I wanna do that again.” She said.

“Right now?” He said wryly.

“No, but soon. There’s something about you that just drives me crazy.” She said.

“Is it my money?” He asked.

Liz gave him a stern look.

“ _No._ ” She said.

“My penis?” He joked.

“No, well, _yes_ …but I mean, I’m so attracted to you, it’s insane.” She said, then she kissed him some more.

Liz realized she was in trouble; she was falling for her target. He was her favourite lover and favourite man in general, and she was tasked with pumping him for information. She was more interested in pumping him for fun.

“That’s okay, sweetheart, you drive me crazy, too. We’re probably bad for each other…but in a very pleasant way.” Red said; he was realizing they were both vulnerable to each other. She could make him weak and at risk of divulging secrets, while he could make her fail spectacularly at her mission. It was an interesting conundrum.

“I think you’re right about that.” Liz said.

She gently got off Reddington and went into the en suite bathroom to go pee and tidy herself. She washed her hands and returned to bed.

“Can I cuddle with you?” Liz asked.

“Of course. You don’t have to ask, Lizzie.” Red said.

She smiled and snuggled against him as he pulled the blankets up.

“Are you warm enough?” Red asked softly.

“Yeah.” Liz said.

A couple minutes passed.

“What time should we get up?” Liz asked.

Reddington was quiet, so Liz looked at him; he’d adorably fallen asleep. She smiled and got comfy again, and she soon fell asleep.

(To Be Continued…)

**Notes for the Chapter:**

> As a side note, regarding the show's plot and plans for next season: um, nooo! Why can't you just give us what we want?! The creator/writers/producers seem to be on a completely different wavelength than most fans, and that sucks. I'll still watch it, but I'm going to sulk.  
> Sorry. I had to rant.


	4. Surprises

Liz awoke slowly and peacefully, without her usual beeping alarm. She was cozy and still snuggled against Reddington. She relished this sweet moment, when she didn’t have to worry about her mission. They were just two happy lovers in bed together. Liz stretched and then Reddington woke up; he squinted at the daylight and smiled at her.

“Good morning, Lizzie.” Red said. “Good morning, Raymond.” Liz said.

“How’s my sweet little sugar baby?” He said playfully.

Liz giggled.

“Great! How’s my sugar daddy this morning?” She said, smiling.

“Wonderful. I can’t remember the last time I felt this good.” He said.

Liz smiled and she realized she also couldn’t remember the last time she felt this good. She felt bad for lying to him. She used to feel guilty about not conducting the mission in a more professional manner, but now she felt guilty for taking advantage of Reddington.

“…What would you like for breakfast? I’ll make it.” Liz said.

“Oh, whatever you’re having. I enjoy any kind of breakfast.” Red said.

“Okay, that’s easy. I’ll make toast, coffee and fresh fruit for both of us.” She said.

“Lovely. Thanks.” He said.

“You’re welcome.” She said, then she gave him a soft kiss before getting out of bed.

Red watched Lizzie dig through her luggage bag, then she sighed and looked at him.

“I forgot a robe. I’ll just wear this…” She said, donning his button-up shirt from yesterday.

Red found it adorable that Lizzie put his shirt on; it was like a nightshirt on her. She left the bedroom to head into the kitchen. Red laid there for a few moments longer, wishing this relationship with Lizzie was real. Some of it was certainly real, but would she want to continue like this, if it weren’t for her mission? Would it work? He decided not to dwell on that right now; he threw his boxers and undershirt on, then he washed his hands. He joined Lizzie in the kitchen.

Liz had washed up and now she was trying to figure out how to work the espresso maker. Reddington surprised her by appearing next to her and pressing the correct buttons.

“Thanks.” Liz said wryly.

“No problem.” He said.

Liz resumed peeling the huge juicy orange. The toaster popped, and Reddington grabbed it and put it on the plates.

“I thought I was making breakfast.” Liz protested.

“I don’t want to just sit around while you wait on me.” Red said.

“Fine, you can butter the toast.” She said, smirking.

Red smiled and completed his assigned task, then Lizzie placed the oranges on the plates; he took them to the table while the espresso maker finished. Lizzie delivered their espresso before he had a chance to do it, then they sat down.

“Thank you, sweetheart.” Red said.

“You’re welcome.” Liz said, then they bit into their slices of toast.

“It’s supposed to be perfect weather today, even more perfect than yesterday. Would you like to use the pool, or spend time on the beach?” He said.

“…You want to see my bikini, don’t you.” She said.

“Yes.” He said.

The sheepish smile Reddington gave Liz melted her heart. She really couldn’t understand how this man was the same as the notorious criminal she’d learned about at the FBI. He was so sweet.

“I’ll wear it today. How about we check out the beach?” She said.

“Good idea.” He agreed.

After breakfast, Liz and Reddington took showers, and he dressed in a more casual outfit with a white and beige short-sleeved button-up shirt and tan shorts, while she put her scanty light blue bikini on. Liz felt naked in it, so she wrapped her pretty yellow and blue sarong around her bottom half at first. She put sunscreen and her hat on, then she met Reddington by the back door. He looked her up and down and was flabbergasted.

“My goodness…” Red said.

He was stunned by Lizzie’s beauty and her sexiness. The bikini top was so revealing, it only covered some of her breasts. He was curious to see what the bottoms were like under the sarong. She gave him a coy smile, clearly gratified by his reaction to her.

“You like it?” Liz teased.

“Very much.” Red said.

“Thanks. I like it too.” She said.

Liz shyly took Reddington’s hand and held it.

“Ready? Let’s get some sun and sand.” Liz said.

He smiled warmly at her and they held hands as they stepped out of the building and onto the sandy, grassy path to the shore. They strolled slowly, taking in the gorgeous scenery.

“Thanks again for taking me here, Raymond. It’s so beautiful. This is the best vacation I’ve ever had.” Liz said.

“Oh. You’re welcome. This is my favourite vacation, too.” Red admitted.

“Aww. You’re sweet.” She said indulgently, and he looked adorably sheepish again.

They walked to the water’s edge as it lapped at the sand and their bare feet. It cooled their feet after stepped on the hot sand, but it was mild enough to swim in. Red was amused when Lizzie squealed and jumped away from the tide. There was a large piece of seaweed that startled her. They both laughed.

“I didn’t know what it was!” Liz said.

Red chuckled and put his arm around her waist as they walked. After strolling down the shoreline for some time, Red went over to an incline in the sand and sat down, shaded by trees above. Lizzie stepped closer to him and removed the sarong, revealing her thong bikini bottoms.

“Mm. That is one hell of a swimsuit.” Red said.

“Thank you!” Liz said.

Liz put the sarong down on the ground beside Reddington, then she sat on it and reclined; she took her hat off and put her hand behind her head.

“This is so nice.” She said contentedly.

“It sure is.” He said.

They relaxed like this for quite a while, listening to the waves. Red looked over at Lizzie.

“You know, we have complete privacy. You don’t even have to wear a bikini.” Red said.

Liz laughed.

“Yeah, that’s true. You don’t have to wear anything, either.” She said flirtatiously.

“Good point.” He said.

Red looked down and studied Lizzie’s thong. It was so low-cut in the front, it barely covered her pubic area. It was very alluring. He reached over and put his hand on her tummy, then he stroked along the top of her bikini bottoms.

“That tickles…” She purred.

“Mmm.” He responded lustfully.

Red traced the line of her top and it seemed to tickle her, too; she shivered slightly and her nipples became hard under the thin material. He leaned closer and kissed her temple, then she turned her face towards him and kissed him. Liz felt Reddington’s hand softly trail down her tummy. His fingers lightly stroked her crotch in a tantalizing manner, overtop the swimsuit material.

“Mm…I love how you touch me…” Liz said softly.

“I love touching you.” Red said quietly.

Liz smiled and turned towards Reddington; she leaned against him and kissed him. They kissed and she was getting very aroused, so she was disappointed when he stopped.

“Remember how I said we have complete privacy? Well, there’s a drone coming towards us.” Red said.

“What?!” Liz said, startled.

She looked up into the sky and saw a small flying object coming over the water towards the island. Reddington took a gun out of the back of his shorts and aimed steadily, waiting for it to get closer. She was surprised he was armed this whole time during a romantic stroll on the beach, but she supposed he was right to be cautious.

“It’s not one of yours, is it?” Red asked, still taking aim.

Liz knew the top secret task force wouldn’t do anything so obvious.

“No—wait, what?! Why would I have a drone?!” Liz said, realizing her cover might be blown.

The drone was within shooting range, so Reddington fired; the drone was hit and dropped into the ocean. They didn’t see anything else; it must have come from somewhere a good distance away. Reddington lowered his gun and looked at her.

“I’m assuming it wasn’t an FBI drone…Which means we should pack up and go elsewhere for safety.” Red said.

Liz gaped at him.

“How would I know about drones and the FBI?” Liz said.

Reddington gave her a sly smirk; her cover was blown. She gave up.

“Um…are you angry with me? I didn’t send the drone, and I wasn’t going to arrest you, I was just supposed to get some intel, but I really like you. I can’t go through with my mission, even if I _could_ get intel out of you, which I _can’t_ …What I feel for you is real—” Liz rambled nervously.

Reddington put his hand up to quiet her, so she stopped talking.

“Lizzie, I’m not angry. This was no big surprise or betrayal…I knew the entire time, ever since you walked into the party.” Red said.

“…Huh? How?” Liz asked.

“It’s a bit of a long story, and I’m afraid we have to get moving. Let’s go grab our things and go back to the jet. I’ll text the pilot.” He said, getting up and dusting sand off his butt.

Liz was still in shock, but she could tell that Reddington wasn’t a threat to her, so she stood and picked up her sarong and her hat. She followed him to the resort building, where they quickly gathered their belongings and took their luggage. Liz felt sad because they had to leave this perfect island, and even worse, since her cover was blown, her mission was over and she’d no doubt have to leave Reddington. She was quietly crying by the time they reached the jet. Red turned to Lizzie to allow her to climb the steps first, and he noticed she was crying.

“Oh sweetheart, what’s wrong?” Red said.

Liz sniffled and took a deep breath so she could talk.

“I don’t want to leave you.” Liz said.

“You don’t have to leave me. We’re heading home together, on the same jet.” He said.

“But my mission failed and now I’m gonna have to let you go.” She said sadly.

“You don’t have to, Lizzie. We can still be together if you want to.” He said, cupping her face in his hands.

She looked at him with sorrowful, watery, blue eyes.

“Come here, baby. I’m not leaving you.” Red said softly as he embraced her.

Liz clutched Reddington tightly; she realized just how much she’d fallen in love with him. She couldn’t stand the thought of their relationship ending.

“Come on, let’s get going. When we arrive back in the States, we can go to my safe house together, alright?” Red said.

Liz sniffled as they pulled apart, then she nodded and went up the steps into the jet. She had to grab a tissue and blow her nose. She felt Reddington’s hand on her back, giving her a comforting rub.

“I meant what I said earlier. I really like you, Raymond.” Liz said as they sat down next to each other in the seats.

“I know. I really like you too, Elizabeth.” Red said with a gentle smile.

“…How did you know my identity? We have time for your story now.” She said.

Red paused and thought about what he would say.

“You won’t remember, but when you were little, and you got that scar…I was there. I took you out of the burning house.” Red said quietly.

Liz was dumbfounded; she gaped at Reddington, trying to process all this. He not only knew her identity but he saved her as a child?!

“…For real? You’re not making that up?” Liz asked.

“For real. And afterwards, I decided to keep tabs on you. I followed your life and career.” He said nostalgically.

“I had no idea, about any of it.” She said, staring at him.

Red nodded subtly.

“Thank you for rescuing me from the fire. I can’t believe I ended up on a task force mission to track you down and get intel from you.” She said.

“You don’t have to thank me. But yes, I agree it’s an interesting twist of fate.” He said.

Lizzie intertwined their arms and rested her head on his shoulder. They sat in silence like this for a long time. Eventually, the jet landed on a remote private airstrip and they took their luggage to the waiting car. One of Red’s drivers took them to his safe house and unloaded their luggage for them. They got settled in and ate a meal together, then they went to bed early, as they were exhausted.

~ ~ ~ ~ ~ ~

Liz woke up in the morning, hearing some distant traffic and she recalled they were no longer on the island. As much as that disappointed her, she felt better as she also recalled she was in Reddington’s bed at his safe house. She felt him spooning her with his arm around her waist. She arched and pushed her butt against him and he started to become hard. Liz moaned quietly and squirmed to try and feel his erection between her legs. Red was pleasantly surprised to wake up to Lizzie grinding into him; he was ecstatic and ready to go. Red reached down and guided his erection between Lizzie’s legs and rubbed against her very moist flesh. She whimpered in pleasure.

“Is this what you want, baby?” Red rumbled.

“Yes!” Liz breathed.

Red squeezed into Lizzie’s tight entrance and he paused for her to adjust. He massaged her breast and lightly rubbed her nipple. Liz was so horny, she quickly became fully aroused and relaxed enough for Reddington to thrust deeper. He felt amazing inside her. He filled her perfectly and stimulated her g-spot. She arched her back and lifted her leg up higher, easing his movements. Red felt that Lizzie was very slippery, and she was mewling and writhing in pleasure. 

“Yeah, that feels good, doesn’t it Lizzie…” Red said seductively.

“Oh god yes…” Liz purred.

“I want to fuck you harder…do you want that?” He said lustfully.

“Yes, Raymond…please…” She urged.

Liz felt Reddington’s grasp on her hip tighten and he pulled her each time he thrust into her. They breathed heavier and reached up to hold onto the headboard; she pushed her butt back towards him, bracing against his rough thrusts. Red groaned and revelled in the feel of Lizzie’s walls tightening on his cock. She was mewling breathlessly and getting even wetter.

“Wait, I’ll lay on my front.” Liz said.

“Okay.” Red said.

Liz felt Reddington pull out and she missed him already; she quickly laid on her tummy with her legs parted. She was thrilled when Reddington mounted her and entered her again.

“Ohhh…” Liz moaned breathily.

Red was in an easier position now, so he could thrust quickly. He held onto the headboard for leverage and he felt Lizzie stick her butt up. She clutched the headboard and made the sweetest little whimpers.

“ _Lizzie_ …mm…” Red grunted intensely.

Liz was in mind-numbing pleasure as Reddington hit her g-spot every time he went in. He was at the perfect angle. She trembled and became breathless again. Reddington teased her by slowing down and giving her long, deep thrusts. She could feel every inch of his cock. Liz whined in both ecstasy and desperation; this was exquisite torture, so heavenly and yet she needed satisfaction. Reddington quickened his pace again and she could feel them becoming more lubricated from his pre-ejaculate fluid. Liz was shaky and almost seeing stars as she neared the peak.

Red was on the verge of coming; he listened to Lizzie’s erratic breaths and whimpers, and the wet sounds from their lovemaking. He felt her slick walls pumping and tugging his cock as she tensed up. Lizzie cried out and then writhed under him, muffling her whines in the pillow as she orgasmed. Red paused for a moment to focus on the sensation of her wetness undulating on his cock. He moaned and bucked his hips, nudging her very tight walls until he came explosively. He groaned and felt the most intense pleasure as he spilled into her.

Liz was experiencing lingering arousal, and a lot of gratification from having Reddington come inside her. She arched her back and pushed her butt against him, wanting more. While he caught his breath, he reached down to her hip and tried to slide his hand underneath her. They both lifted up slightly to accommodate his hand, then he began wiggling his fingers on her clit while his cock remained inside her.

“Oh!” Liz responded; she was overly sensitive but after several moments, the pleasure was building towards a climax.

Red slipped in and out of Lizzie a little bit while he fingered her clit, and she clawed the bed and panted. About a minute later, she had her second orgasm. Afterwards, Lizzie slumped relaxedly and sighed. He waited a few moments, then he kissed her on the head and got off her; he laid down on his back.

“Oh my god Raymond, that was just…wow.” Liz said.

“It _was_.” Red agreed with a smirk.

They basked in their satisfaction for a couple minutes.

“Should I make pancakes?” Red asked.

“No thanks, I actually don’t like pancakes.” Liz said.

“How could you not like pancakes?” He teased.

“I dunno!” She laughed.

“How about waffles then?” He asked.

“Waffles are good.” She said.

Red smiled amusedly and got out of bed to make waffles for breakfast.

(To Be Continued…)


	5. Turbulence, Then Calm

**Notes for the Chapter:**

> I got inspiration from a comment about where to take the story. Thank you! 
> 
> Tags for this chapter: Romance, Angst, Feelings, Fluff and Happy Ending
> 
> I hope you enjoyed this fic. I'm sure I'll dream up another Lizzington story soon. :)

After breakfast, Liz shyly brought the diamond necklace to Reddington.

“I’m not sure if I should have this. I was just playing the sugar baby character.” Liz said.

“I gave it to you because I truly wanted you to have it, Lizzie. I knew you weren’t actually a sugar baby, although, you played the role quite convincingly. It was rather fun.” Red said, then he smiled.

Liz chuckled.

“Thanks, Raymond. If you’re sure, then I’ll keep it.” She said.

“I’m certain.” He said.

“Okay. I appreciate it. It’s my favourite necklace, because you gave it to me.” She said softly; she placed the necklace on the dining table, where she wouldn’t lose it.

“You’re a sweetheart. By the way, do you really have student loans you still need to pay off?” He said.

“Yeah, but you don’t have to—” She was saying.

“I’ll pay them off. You don’t have to give me the loan account numbers, I can find that out.” He interrupted.

“No, it’s a lot of money.” She said stubbornly.

“A university education is not a lot of money to me. It’s like pocket change. As I said, I’m going to take care of it for you.” He said.

Liz and Reddington stared at each other; they were both very stubborn, but in this instance, Liz decided to back down.

“I know you’re going to do it even if I say not to, so I might as well give you permission. I’ll give you the account numbers.” She said, smirking.

“Great!” He said, clapping his hands together excitedly.

Liz laughed.

“You’re happy to pay off someone else’s debt?” She said amusedly.

“ _Your_ debt, yes.” He said, pleased to get his way.

Liz smirked and signed into her student loan account on her phone. She handed him the phone and he called someone on his burner phone.

“Yes, I’d like to…oh, sorry, I forgot it’s four a.m. where you are. I need you to do something for me. You’re too kind. Please use clean money to pay the following account balances as an anonymous benefactor…” Red said, then he listed the account numbers.

Liz glanced down at her phone screen and she was shocked to find that Reddington made her student debt magically disappear. The accounts showed the payments in full and balances of $0 owed. He thanked the person and his phone clicked shut. Liz looked at him and he was smiling.

“I can’t thank you enough, Raymond. It’s gonna look suspicious if the task force catches wind of it, though.” Liz said.

“Not to worry. You can say you needed to go that far in your sugar baby role. You had no choice.” Red said.

“Hmm. Yeah, I guess so.” She said.

Liz was feeling conflicted again; she felt like a double agent now that she was in a relationship—a real one—with Reddington. Red noticed that Lizzie was getting that distant look in her eyes, probably feeling guilty again.

“Let’s have a shower together.” He said, distracting her from her thoughts.

“Oh. Okay.” She said.

Red ushered Lizzie into the bathroom and he dropped his boxers; now she was _really_ distracted from her thoughts. She blushed lightly as she realized she was staring at his manhood. He enjoyed the way she looked at him. Liz took her pyjama t-shirt and shorts off, then Reddington turned the shower on and they stepped in. They washed and rinsed, and Liz was no longer worried or conflicted. She felt rejuvenated and happy; she was in love and she just had her student loans paid off. She stepped closer, put her hands on Reddington’s cheeks and gave him a big kiss.

“What was that for?” Red asked.

“Everything.” Liz said.

“Oh alright.” He said, then he kissed her; he felt her smile against his lips.

They kissed a few more times, then they got out of the shower and dried off. Liz contemplated what she was going to do. She had almost unlimited time to complete her mission, but she’d failed it. She couldn’t continue spending time with Reddington just for fun, all the while deceiving the task force. She would have to fess up to the bungled mission. Liz was worried that it would mean never seeing Reddington again while some other, perhaps more competent, agents chased him. After getting dressed in jeans and a tank top, Liz sat on the bed and just stared anxiously at the floor.

“Are you alright?” Red asked.

“No. I have to update the task force about my failed mission, and I’m scared something bad will happen to you. Not to mention they’ll give me a desk job for the rest of my career.” Liz said.

Red stepped closer and sat next to Lizzie on the bed.

“Can you put it off a little while longer? I will work on some things and come up with a plan.” Red said.

“What kind of plan?” She asked.

“Something that will ensure we can stay together. I just need time to think and to get my business affairs in order.” He said.

Liz liked the sound of the plan.

“How long would it take?” She asked.

“…Several weeks, perhaps a month at the most.” He said.

Liz raised her eyebrows; that was much longer than she expected.

“Please, Lizzie? Can you do this for me? I promise that after I finish my tasks, we’ll be able to stay together and you’ll keep your crime-fighting career.” Red said earnestly.

Liz took a minute to consider it. Pretending she was still on the mission for maybe a month would be bad, but it would be worth it if she and Reddington could have the best of both worlds—their relationship and her career.

“Okay. I’ll do it.” Liz said.

Red was ecstatic. He put his arm around Lizzie and kissed her. He would find a way for everything to work out.

**~ ~ ~ ~ Five Weeks Later ~ ~ ~ ~**

Liz and Reddington had been living together in his safe house and he’d been busy attending to his business, which she didn’t ask about. She didn’t get in touch with Ressler or Cooper yet; she basically continued living as a sugar baby, including lounging around the safe house in expensive lingerie that Reddington bought for her. Liz was bored, but she kept reminding herself this would all be worth it. She occasionally asked him about his progress and he said he was nearly finished.

Reddington was out again on secret errands and Liz was trying to keep herself occupied, especially since she was worried about how late her period was. She tried to rationalize it and put it out of her mind, but she couldn’t. Her periods were normally regular as clockwork, and she felt a bit different the past few days. She wasn’t as hungry, and she no longer craved coffee. Liz finally decided to face the issue head-on; she got dressed and called one of Reddington’s drivers for a ride to a nearby drugstore. She asked the driver to wait, then she went in and found the family planning aisle. Liz felt a bit faint as she surveyed the pregnancy tests; she wondered if that was another sign of pregnancy, or just her anxiety. She realized she’d barely breathed since she got in the aisle, she was so panicked. Liz took a few deep breaths and then shakily reached for a pregnancy test kit. She went to the counter and bought it, then she hid it in her purse as she returned to the waiting car. She asked the driver to take her back to the safe house.

Once inside, Liz checked to see if Reddington was home, but he wasn’t. She carried the test kit into the bathroom and read the instructions, even though she could barely focus. She had to go pee, so she was able to pee on the stick. Then she endured the most nerve-racking wait of her life. Liz set her phone timer and when it beeped, her heart skipped a beat and she wondered if she had the courage to look at the results. She did some more deep breathing and then snatched the test off the counter, quickly bringing it up to view the results window. Liz leaned against the vanity and dropped the test into the sink by accident. It was positive. Liz was in shock; she had to double- and triple-check the results. Her next reaction was to start bawling her eyes out. This was the most conflicted she had ever felt; she loved the idea of having Reddington’s baby, but she felt like it could never work, with who they were. Their paths led in separate directions, and whatever his plan was that he was working on, a baby would surely get in the way of it. Who were they to think they could be together? An FBI agent and crime lord? Not to mention it had been five weeks and Reddington still wasn’t done sorting things out with his business. Liz was heartbroken, but she felt like it was time to come back to reality and come to terms with the fact that their relationship was just a brief, beautiful encounter.

After hours of crying and thinking, Reddington still wasn’t back, so Liz packed up her things. She grabbed a piece of paper and a pen. Through tear-blurred eyes, she wrote a note to Reddington. Several tears dropped onto the paper, smudging the ink. She then left the safe house before she changed her mind. Liz had no other transportation, so she called the driver again. She didn’t want to risk leading a taxi to the safe house. She got into the car and asked to be taken to the airport.

~ ~ ~ ~ ~ ~

Red had finally finished putting his business affairs in order and he excitedly arrived home to the safe house, ready to announce the final phase of the plan to Lizzie. However, when he went inside, he called for her and there was no answer. Some of her belongings were gone, so he frantically searched for a note, which he found on the dining table. His heart pounded as he picked it up and read it:

_Dear Raymond,_

_We have to realize this isn’t going to work. I love you and I’ll miss you, but I have to go back home and face reality. I’m sorry that the plan didn’t work out, and I’m sorry to leave you like this. It’s probably for the best. Especially now. I’d just be a burden. I wish things were different, but they’re not._

_Love always — Lizzie_

Red’s heart sank into his stomach and he had to dab his eyes with his handkerchief. He was pained by the letter and by seeing the tear-stained paper from Lizzie crying over it. He refused to give up and let her go like this. Things _could_ work between them, now that the plan was in place. What did she mean ‘especially now’ she’d be a burden? He wondered. Red grabbed his phone and called the number for whichever chauffeur was on duty.

“Where did she go?” Red said as soon as someone answered.

“Uh—I dropped her off at the airport forty-five minutes ago, Sir. Before that, she went to the drugstore.” The driver reported.

Red fumbled slightly, nearly dropping his phone.

“Get here and take me to the airport now!” Red shouted urgently, then he raced outside to wait anxiously for his ride.

When the car pulled up, Red jumped into the backseat and the driver stepped on the gas pedal. They drove as fast as possible without risking a speeding ticket. Red felt hopeless as they arrived at the airport about an hour after Lizzie would’ve gotten there, but he had to try. He ran in, wearing his hat and sunglasses to avoid being recognized on surveillance cameras. Red jogged over to the waiting area and quickly surveyed the people on benches and in lineups for tickets. He then checked the lineup of passengers ready to board the jet. He was crestfallen as he didn’t find her. When he gave up and turned around, his heart sang as he spotted Lizzie standing by a window with her luggage bag; she was dabbing her eyes with a tissue.

“Lizzie!” Red called.

Liz was startled and very surprised as she whirled around to see Reddington approaching her. She was both worried and happy to see him. He came up and embraced her tightly. After a few moments, she hugged him back, and she started crying all over again. They eventually released each other.

“What are you _doing_ , sweetheart?” Red asked.

“I froze and couldn’t leave…I was waiting for a later flight. I needed more time to think.” Liz explained.

“But why are you leaving?” He asked.

“…You got my note? It can’t work between us…” She said.

“I got your note. It broke my heart.” He said.

Liz covered her face with her hands and sobbed.

“I’m sorry.” She said.

“Shh it’s okay. Is that the only reason? You think we can’t be together? Or...do you not want to be with me anymore?” He said.

“Raymond, I _love_ you. I want to be with you, it’s just we’re from two different worlds. You tried to come up with a plan, but that’s not gonna work either. I’ll need a desk job.” She said.

“It’s finished. It will work, but…why do you need a desk job? And why did you go to the drugstore earlier? Are you ill? You said you’d be a burden.” He said worriedly.

Liz couldn’t hide the truth from Reddington any longer; he was the baby’s father. Plus he was clearly thinking she was seriously ill and she needed to set his mind at ease.

“I’m…pregnant…” Liz said in a small voice.

Red barely heard Lizzie, but he did. He was shocked and overjoyed, and perplexed as to why she’d take off on a jet.

“Elizabeth. That’s incredible news.” Red said dazedly.

“Is it?” She asked nervously.

“Yes! Why on earth would you leave now, thinking you’d be a burden?” He said.

“If our relationship couldn’t work with just the two of us, then how would we deal with a baby?” She said.

“Our relationship can work, and we’ll deal with a baby like any other proud parents do.” He said, now smiling.

“…What’s your plan? You said it’s done?” She asked.

“We both go back to the task force. You didn’t bungle the mission, you turned me. I’ll be an informant, as long as I get to give my intel to you. We can both have desk jobs! And bring the baby to work!” He said happily.

Liz couldn’t help smiling at the thought.

“Really?” She asked.

“Yes, sweetheart. Would you like to do that?” He said.

Red waited nervously for Lizzie’s decision.

“Wait, are you sure you won’t be arrested and kept in a black site?” She asked.

“Yes. I’ll make a deal with them, and you can be my handler. Well?” He said.

Liz thought for a few moments longer, then she smiled.

“Okay!” She agreed.

“Oh, thank goodness. I thought I was going to lose you. I couldn’t bear it, Lizzie.” He said, wrapping his arms around her and kissing her on the head.

“I couldn’t bear it either, but I thought I had to.” She said.

“No. Everything will be fine. Now let’s rip up that ticket and take my jet instead. When we get back, you can contact your superiors and arrange for all of us to meet.” He said.

“Okay. Let’s do it.” She said.

~ ~ ~ ~ ~ ~

On the flight to Lizzie’s home city, with her real apartment and task force, Red held her against him as she napped. He couldn’t stop thinking about her being pregnant; he was going to be a dad. His beloved Lizzie was carrying precious cargo in her tummy. He smiled and barely stopped smiling until they landed. Red couldn’t remember the last time he’d been so happy. Liz woke up and smiled at Reddington, who looked pleased as punch. She chuckled.

“I’m going to be a daddy. Not just a sugar daddy.” Red said humorously.

Liz laughed.

“Yes, you are. And you’re going to be the sweetest daddy.” Liz said, then she kissed him.

“Thank you.” He said.

They made their way to the car and rode in the back together, then they took their luggage into Liz’s apartment.

“Well, this is my _real_ apartment.” Liz said wryly.

“It’s nice. I like it. Of course, we’ll have to move into something larger, with a nursery and lots of room to expand.” Red said.

Liz found it adorable that Reddington was so excited about the pregnancy. She couldn’t be happier, now that she knew it was possible to be a couple and raise the child together.

“I love you, Raymond.” Liz said.

“I love you too, Lizzie.” Red said.

“Do you forgive me for almost running away?” She asked.

“Yes. You were overwhelmed and you didn’t see how our lives could match up. I understand.” He said.

“Thanks.” She said sheepishly.

“Let’s order pizza, and then you can call your people.” He said.

Liz nodded.

They had pizza delivered for their late supper and then sat on the couch together. Liz nervously made the call to Ressler.

“Ressler? The mission has taken a different direction, but I think you guys will be pleased.” Liz said.

“Oh? What’s going on?” Ressler asked.

“Reddington has agreed to be an informant for us. He’s sitting next to me right now. We’re back at my apartment—my real apartment.” She said.

There was stunned silence on the line for several moments, and Liz glanced at Reddington.

“Ressler?” Liz said.

“Yeah, I’m just shocked. Uh…wow. Okay. That’s definitely not what we were expecting, but it’s even better!” Ressler said.

“Yeah, but he has certain conditions that have to be met.” Liz said.

“Of course he does.” Ressler said.

“He needs immunity and pardons; he’ll get to start from a clean slate.” Liz said.

“Um…” Ressler said.

“That’s non-negotiable. It’s also important to me that he gets a fresh start. We’ve uh…formed a very strong bond…” Liz said.

“Is that so?” Ressler asked.

“Yes.” Liz said firmly.

“Alright, Cooper’s saying we’ll make the deal. We want his intel.” Ressler said.

“Okay, great! Um…this job has parental leave, right?” Liz said.

“….Yeeeeaaaah…Why are you asking about that?” Ressler said, dreading her answer.

“I just found out I’m pregnant, and Reddington and I are planning for our future.” Liz said.

Red smiled and rubbed Lizzie’s back; he was proud of her for being assertive and admitting the truth.

“Wow. Uh congratulations? You can request parental leave for both of you later on, when it gets closer to the time.” Ressler said uncomfortably; Agent Milhoan was having Reddington’s baby?!

“Sounds good. Thanks, Ressler. I’ll get in touch again maybe tomorrow to check on Reddington’s deal and then we can all meet.” Liz said.

“Alright. Talk to you soon. Bye.” Ressler said, then they hung up.

Liz was amused by Reddington’s playful, optimistic smile.

“So everything went perfectly!” He said.

Liz chuckled.

“Yeah. It’s all okay, despite Ressler’s disapproval on a personal level.” She said.

“Wonderful.” He said, then they kissed.

“Can we sleep now? I’m exhausted.” She said.

“Of course, baby.” He said.

They got up and turned the lights off, then they went into the bedroom. They both took all their clothes off and then they snuggled in bed together; they soon fell asleep.

** Epilogue**

Liz and Reddington met with the task force and he got the deal he wanted. They worked with the task force on a regular basis, mainly in the black site, especially as Liz’s tummy grew and she was closer to going on parental leave. Red wanted to go on parental leave, too, and he could afford to support their little family without shifts at the black site. Shortly before Lizzie’s due date, they went on leave together and finished preparing the nursery in their new, spacious safe house. Liz went into labour two days early, at one in the morning; she and Reddington rushed off to his medical team’s facility, which was surprisingly inviting and comfortable. He’d made sure to have it set up as any typical maternity ward plus midwives, which Liz appreciated. The labour was short, as their baby seemed to be in a rush to meet the world. Liz gave birth to a baby girl. The tiny bundle of joy was first handed to her as the mom, but she knew Red was eager to hold her, so she passed the baby to him. Liz cried tears of joy as she watched Reddington cradle their daughter; he had such a proud, amazed expression on his face, it made her heart soar. It was the cutest sight she’d ever seen, Reddington being enthralled with their adorable baby. They watched raptly as their daughter blinked and yawned and fell asleep in his arms. They named her Angelica, and she was the light of their lives. Liz and Reddington took an adorably sleepy Angelica in her carrier to meet Ressler and Cooper. They fell in love with her despite their initial disapproval about the union between informant and agent. They gave her a baby-safe plush frog and a high-tech baby monitor system courtesy of the FBI. Red and Lizzie navigated life with a newborn baby and they managed to enjoy everything about it. They also continued to enjoy private moments together, when they had the chance, which reminded them of the fun, flirtatious start to their relationship. They still joked about being a sugar daddy and sugar baby.


End file.
